EP0856565A1 - Ink composition for a meltable ink - Google Patents
Ink composition for a meltable ink Download PDFInfo
- Publication number
- EP0856565A1 EP0856565A1 EP98200284A EP98200284A EP0856565A1 EP 0856565 A1 EP0856565 A1 EP 0856565A1 EP 98200284 A EP98200284 A EP 98200284A EP 98200284 A EP98200284 A EP 98200284A EP 0856565 A1 EP0856565 A1 EP 0856565A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ink composition
- weight
- crystalline
- monomer compound
- ink
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
5 122 187. The prior art ink compositions in the set state generally yield on receiving materials printed ink layers which are too brittle or just too soft, with the result that the gum, scratch and fold resistance, particularly of double layers, i.e. different ink layers of, for example, different colours on one another, is not up to standard. To toughen ink formulations which are too brittle, or make too soft crystalline materials stiffer, the addition of an amorphous binder is necessary, with or without the combination of a monomer plasticiser. However, as a result of the considerable viscosity increase in the melted state, caused by such an addition, only a low concentration (up to about 20% by weight) of amorphous polymer or oligomer binder can be used.
US-5 421 868 and from the symmetrical bis-amides and bis-sulphonamides. It is possible to use mixtures of the above compounds.
Rapidly setting crystalline monomer (25 - 45% by weight), e.g. 1,12-dodecane diol), amorphously setting monomer (45 - 65% by weight, e.g. pentaerythritol tetrabenzoate) and 5 - 10% by weight of amorphous polymer or oligomer binder, e.g. Kunstharz SK (™ Hüls).
Selection of amorphous oligomer/polymer (AOP) | ||||||
No. | Name (trade name) (Abbreviation) | Chemical description | TG (°C) | Mw (g/mol) | η 150°C (mPa.s) | Assessment |
A | Foral 85E (Hercules™) (F85E) | Glycerol ester of hydrogenated rosin | 37 | 1000 | 250 | Little stiffening action |
B | Foralyn 110 (Hercules™) (F110) | Pentaerythritol ester of hydrogenated rosin | 54 | 1300 | 500 | Little stiffening action |
C | Uratak 68520 (DSM™) (U68520) | Phenolic poly-α-methyl styrene | 37 | 880 | 350 | Little stiffening action |
D | Crystalbond 509 (Printlas™) (CB509) | Polyethylene phthalate | 30 | 4000 | 1000 | Usable |
E | (Aldrich) (PSAA) | Styrene allyl alcohol copolymer | 59 | 1600 | 3000 | Usable |
F | Dynacoll 7130 (Hüls™) (D7130) | Copolyester | 27 | 7100 | 3400 | Usable |
G | Dynacoll 7150 (Hüls™) (D7150) | Copolyester | 46 | 6100 | 7500 | Usable |
H | Kunstharz AP (Hüls™) (KHAP) | Acetophenone formaldehyde condensation product | 47 | 1100 | 500 | Little stiffening action |
I | Kunstharz SK (Hüls™) (KHSK) | Reduced acetophenone formaldehyde condensation product | 89 | 1350 | 25000 | Usable |
J | Kunstharz CA (Hüls™) (KHCA) | Cyclohexanone aldehyde condensation product | 69 | 1050 | 5000 | Usable |
K | Kunstharz EP-TC (Hüls™) (KHEP) | Ketone aldehyde condensation product | 28 | 750 | 140 | Little stiffening action |
Claims (11)
- An ink composition for a meltable ink, usable in printing devices in which ink droplets are ejected from ducts, which composition contains a meltable base material, characterised in that the ink composition also contains an amorphously setting monomer compound and an amorphous polymer or oligomer binder and the base material is a crystalline-setting monomer compound.
- An ink composition according to claim 1, characterised in that the amorphously setting monomer compound has a glass transition temperature (Tg) of 10 - 50°C, a viscosity less than 100 mPa.s at 150°C and has a molecular weight lower than 1000.
- An ink composition according to claim 1, characterised in that the amorphous polymer or oligomer binder has a Tg between 25 and 120°C, a weight-averaged molecular weight of between 1000 and 15000 and a viscosity greater than 1000 mPa.s at 150°C.
- An ink composition according to claim 1, characterised in that the crystalline-setting monomer compound has a melting point lower than 110°C and a viscosity at 150°C of 1 - 10 mPa.s.
- An ink composition according to claim 1 or 2, characterised in that the amorphously setting monomer compound is selected from the group of bis-urethanes, esters of pentaerythritol and dipentaerythritol, carbonates of dipentaerythritol, bis-amides, bis-sulphonamides and reaction products of epoxides and alcohols.
- An ink composition according to claim 1, characterised in that the quantity of crystalline-setting monomer compound is between 60% by weight and 90% by weight, the quantity of amorphously setting monomer compound is between 5% by weight and 20% by weight, and the quantity of the amorphous polymer or oligomer binder is between 5% by weight and 20% by weight, based on the total ink composition, the difference between the melting temperature and the crystallisation temperature of the crystalline-setting monomer being less than 50°C.
- An ink composition according to claim 1, characterised in that the quantity of crystalline-setting monomer compound is between 25 and 45% by weight, the quantity of amorphously setting monomer compound is between 45% by weight and 65% by weight, and the quantity of the amorphous polymer or oligomer binder is between 5% by weight and 10% by weight, based on the total ink composition, the difference between the melting temperature and the crystallisation temperature of the crystalline-setting monomer being less than 25°C.
- An ink composition according to any one of the preceding claims 1, 2, 5, characterised in that the amorphously setting compound is selected from the group: the reaction product of isophorone diisocyanate with methyl alcohol or the reaction product of 4,4'-dicyclohexylmethane diisocyanate with benzyl alcohol, the benzoate, toluate and anisilate esters of penta-erythritol and dipentaerythritol, phenyl carbonates or substituted phenyl carbonates of dipentaerythritol, reaction products of propoxylated bisphenol A with alkyl or cycloalkyl substituted phenols.
- An ink composition according to any one of the preceding claims 1 and 4, characterised in that the crystalline-setting monomer compound is selected from the group: alcohols, sulphonamides, bis-urethanes and amides.
- An ink composition according to claim 9, characterised in that the crystalline-setting monomer compound is selected from the group: dodecanediol, hexadecanediol, para-toluene sulphonamide, para-ethylbenzene sulphonamide, para-n-butylbenzene sulphonamide, 1-O-para-anisyl glycerol, meta-toluamide, the reaction product of hexamethylene diisocyanate and 2-methoxyethanol or is a mixture of these compounds.
- An ink composition according to any one of the preceding claims, characterised in that the viscosity of the total ink composition is lower than 25 mPa.s at 130°C.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL1005174A NL1005174C2 (en) | 1997-02-04 | 1997-02-04 | Ink composition for a fusible ink. |
NL1005174 | 1997-02-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0856565A1 true EP0856565A1 (en) | 1998-08-05 |
EP0856565B1 EP0856565B1 (en) | 2004-04-28 |
Family
ID=19764337
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98200284A Expired - Lifetime EP0856565B1 (en) | 1997-02-04 | 1998-01-29 | Ink composition for a meltable ink |
Country Status (7)
Country | Link |
---|---|
US (1) | US6071986A (en) |
EP (1) | EP0856565B1 (en) |
JP (1) | JP4420988B2 (en) |
CA (1) | CA2228740C (en) |
DE (1) | DE69823399T2 (en) |
ES (1) | ES2221114T3 (en) |
NL (1) | NL1005174C2 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1033222A1 (en) * | 1999-02-25 | 2000-09-06 | 3D Systems, Inc. | Phase change compositions and methods for selective deposition modeling |
EP1067157A1 (en) * | 1999-07-09 | 2001-01-10 | Océ-Technologies B.V. | Ink composition for a meltable ink and a method of printing a substrate with such an ink composition |
NL1017049C2 (en) * | 2001-01-08 | 2002-07-09 | Ocu Technologies B V | Ink composition for a meltable ink. |
US6692668B2 (en) | 2001-05-21 | 2004-02-17 | Oce-Technologies B.V. | Method for manufacturing pellets of hot-melt ink |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL1009791C2 (en) * | 1998-08-03 | 2000-02-04 | Oce Tech Bv | Ink composition for a fusible ink. |
ATE260310T1 (en) * | 1999-06-21 | 2004-03-15 | Surface Specialties Austria | WATER-DILUTIBLE RESINS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
US6414051B1 (en) * | 2000-02-01 | 2002-07-02 | Xerox Corporation | Acoustic printing inks containing bis(carbamates) |
NL1020682C2 (en) * | 2002-05-27 | 2003-11-28 | Oce Tech Bv | Fusible ink composition. |
NL1021011C2 (en) * | 2002-07-05 | 2004-01-06 | Oce Tech Bv | Fusible ink for an inkjet printer and a method for selecting such an ink. |
US6960248B2 (en) * | 2003-05-22 | 2005-11-01 | Arizona Chemical Company | Cyclic bisamides useful in formulating inks for phase-change printing |
EP1846206B1 (en) | 2005-02-04 | 2008-04-23 | Océ-Technologies B.V. | Method and mould for manufacturing pellets of hot-melt ink |
EP1995434A1 (en) * | 2007-05-25 | 2008-11-26 | Magneti Marelli Powertrain S.p.A. | Control method in the case of a fault in an internal combustion engine fitted with a servo-assisted butterfly valve |
US8506040B2 (en) | 2011-04-27 | 2013-08-13 | Xerox Corporation | Solid ink compositions comprising crystalline-amorphous mixtures |
US8465579B2 (en) | 2011-04-27 | 2013-06-18 | Xerox Corporation | Solid ink compositions comprising crystalline esters of tartaric acid |
US8372189B2 (en) * | 2011-04-27 | 2013-02-12 | Xerox Corporation | Phase change inks and methods of making the same |
US8690309B2 (en) * | 2011-04-27 | 2014-04-08 | Xerox Corporation | Print process for phase separation ink |
US8833917B2 (en) | 2011-04-27 | 2014-09-16 | Xerox Corporation | Solid ink compositions comprising crystalline-amorphous mixtures |
US8500896B2 (en) | 2011-04-27 | 2013-08-06 | Xerox Corporation | Solid ink compositions comprising amorphous esters of tartaric acid |
US8287632B1 (en) | 2011-04-27 | 2012-10-16 | Xerox Corporation | Solid ink compositions comprising amorphous esters of citric acid |
US8308859B1 (en) | 2011-04-27 | 2012-11-13 | Xerox Corporation | Phase change ink components and methods of making the same |
US8506694B2 (en) * | 2011-04-27 | 2013-08-13 | Xerox Corporation | Phase separation ink |
US8328924B2 (en) | 2011-04-27 | 2012-12-11 | Xerox Corporation | Phase change inks and methods of making the same |
JP2014527091A (en) | 2011-06-30 | 2014-10-09 | オセ−テクノロジーズ ビーブイ | Hot melt ink composition containing copolyester and process for preparing copolyester |
JP6174595B2 (en) * | 2011-12-09 | 2017-08-02 | オセ−テクノロジーズ・ベー・ヴエーOce’−Nederland Besloten Vennootshap | Hot melt cleaning composition, method for preparing hot melt cleaning composition and use thereof |
US9528016B2 (en) * | 2012-04-26 | 2016-12-27 | Xerox Corporation | Phase change inks comprising crystalline amides |
US8882897B2 (en) * | 2012-04-26 | 2014-11-11 | Xerox Corporation | Phase change inks comprising aromatic diester crystalline compounds |
US8888905B2 (en) * | 2012-04-26 | 2014-11-18 | Xerox Corporation | Fast crystallizing crystalline-amorphous ink compositions and methods for making the same |
US8647424B2 (en) * | 2012-04-26 | 2014-02-11 | Xerox Corporation | Phase change inks comprising inorganic nucleating agents |
US8741043B2 (en) * | 2012-04-26 | 2014-06-03 | Xerox Corporation | Bio-renewable fast crystallizing phase change inks |
US8741040B2 (en) * | 2012-04-26 | 2014-06-03 | Xerox Corporation | Phase change ink compositions comprising aromatic ethers |
US8784547B2 (en) * | 2012-06-18 | 2014-07-22 | Xerox Corporation | Lightfast solid ink compositions |
US8851648B2 (en) * | 2012-09-18 | 2014-10-07 | Xerox Corporation | Blends of semi-crystalline materials for inks for direct-to-paper printing |
US8753441B2 (en) * | 2012-11-19 | 2014-06-17 | Xerox Corporation | Bio-renewable phase change inks comprising recycled resin materials |
US8936359B2 (en) * | 2012-11-19 | 2015-01-20 | Xerox Corporation | Ink compositions incorporating ester resins |
US9193883B2 (en) | 2013-06-18 | 2015-11-24 | Xerox Corporation | Phase change ink containing polyester for improved image robustness |
US9447297B2 (en) * | 2013-10-14 | 2016-09-20 | Xerox Corporation | Phase change ink containing amorphous amides |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0404493A2 (en) * | 1989-06-22 | 1990-12-27 | Xerox Corporation | Hot melt ink compositions |
EP0475707A2 (en) * | 1990-09-10 | 1992-03-18 | Seiko Epson Corporation | Hot-melt ink composition |
US5122187A (en) * | 1989-06-22 | 1992-06-16 | Xerox Corporation | Hot melt ink compositions |
EP0610090A1 (en) * | 1993-02-05 | 1994-08-10 | Brother Kogyo Kabushiki Kaisha | Hot melt ink for ink jet printers |
US5421868A (en) * | 1993-12-28 | 1995-06-06 | International Business Machines Corporation | Ink composition |
EP0700977A1 (en) * | 1994-09-02 | 1996-03-13 | Siegwerk Druckfarben GmbH & Co. KG | Hot-melt printing ink |
WO1996015201A1 (en) * | 1994-11-10 | 1996-05-23 | Lasermaster Corporation | Hot-melt ink compositions |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4267000A (en) * | 1979-09-13 | 1981-05-12 | Corning Glass Works | Method for masking glass, glass-ceramic and ceramic surfaces |
DE3545195A1 (en) * | 1985-12-20 | 1987-06-25 | Hoechst Ag | ISOCYANATE-FREE POLYURETHANE DISPERSIONS |
US5006582A (en) * | 1988-08-01 | 1991-04-09 | E. I. Du Pont De Nemours And Company | Acrylic hot melt pressure sensitive adhesive compositions |
US5219657A (en) * | 1988-10-04 | 1993-06-15 | Sumitomo Electric Industries Ltd. | Polyamideimide insulated wire |
JPH0495960A (en) * | 1990-08-08 | 1992-03-27 | Hayakawa Rubber Co Ltd | Composition for photosensitive flexographic printing plate |
US5621022A (en) * | 1992-11-25 | 1997-04-15 | Tektronix, Inc. | Use of polymeric dyes in hot melt ink jet inks |
US5250109A (en) * | 1992-12-22 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Derivatives of polyoxyalkyleneamines as cosolvents for aqueous ink jet inks |
JPH08295836A (en) * | 1995-04-25 | 1996-11-12 | Brother Ind Ltd | Thermally meltable ink |
US5750605A (en) * | 1995-08-31 | 1998-05-12 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on sulfonated polyesters |
US5753017A (en) * | 1995-10-16 | 1998-05-19 | Konica Corporation | Ink jet recording ink and recording method employing the same |
US5667568A (en) * | 1996-03-29 | 1997-09-16 | Xerox Corporation | Hot melt ink compositions |
US5965196A (en) * | 1996-06-14 | 1999-10-12 | Brother Kogyo Kabushiki Kaisha | Method for controlling transparency of print |
US5827918A (en) * | 1996-06-28 | 1998-10-27 | Tektronix, Inc. | Phase change ink formulation using urea and urethane isocyanate-derived resins |
JPH1030072A (en) * | 1996-07-15 | 1998-02-03 | Brother Ind Ltd | Hot-melt ink |
US5855977A (en) * | 1996-08-26 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Multi-layer compositions comprising a fluoropolymer |
-
1997
- 1997-02-04 NL NL1005174A patent/NL1005174C2/en not_active IP Right Cessation
-
1998
- 1998-01-29 DE DE69823399T patent/DE69823399T2/en not_active Expired - Lifetime
- 1998-01-29 EP EP98200284A patent/EP0856565B1/en not_active Expired - Lifetime
- 1998-01-29 ES ES98200284T patent/ES2221114T3/en not_active Expired - Lifetime
- 1998-02-03 JP JP02162598A patent/JP4420988B2/en not_active Expired - Fee Related
- 1998-02-04 CA CA002228740A patent/CA2228740C/en not_active Expired - Fee Related
- 1998-02-04 US US09/018,567 patent/US6071986A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0404493A2 (en) * | 1989-06-22 | 1990-12-27 | Xerox Corporation | Hot melt ink compositions |
US5122187A (en) * | 1989-06-22 | 1992-06-16 | Xerox Corporation | Hot melt ink compositions |
EP0475707A2 (en) * | 1990-09-10 | 1992-03-18 | Seiko Epson Corporation | Hot-melt ink composition |
EP0610090A1 (en) * | 1993-02-05 | 1994-08-10 | Brother Kogyo Kabushiki Kaisha | Hot melt ink for ink jet printers |
US5421868A (en) * | 1993-12-28 | 1995-06-06 | International Business Machines Corporation | Ink composition |
EP0700977A1 (en) * | 1994-09-02 | 1996-03-13 | Siegwerk Druckfarben GmbH & Co. KG | Hot-melt printing ink |
WO1996015201A1 (en) * | 1994-11-10 | 1996-05-23 | Lasermaster Corporation | Hot-melt ink compositions |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1033222A1 (en) * | 1999-02-25 | 2000-09-06 | 3D Systems, Inc. | Phase change compositions and methods for selective deposition modeling |
EP1067157A1 (en) * | 1999-07-09 | 2001-01-10 | Océ-Technologies B.V. | Ink composition for a meltable ink and a method of printing a substrate with such an ink composition |
NL1012549C2 (en) * | 1999-07-09 | 2001-01-10 | Ocu Technologies B V | Ink composition for a fusible ink and a method for printing a substrate with such an ink composition. |
NL1017049C2 (en) * | 2001-01-08 | 2002-07-09 | Ocu Technologies B V | Ink composition for a meltable ink. |
EP1221467A1 (en) * | 2001-01-08 | 2002-07-10 | Océ-Technologies B.V. | Ink composition for a meltable ink |
US6682587B2 (en) | 2001-01-08 | 2004-01-27 | Oce-Technologies B.V. | Meltable ink composition |
US6692668B2 (en) | 2001-05-21 | 2004-02-17 | Oce-Technologies B.V. | Method for manufacturing pellets of hot-melt ink |
Also Published As
Publication number | Publication date |
---|---|
ES2221114T3 (en) | 2004-12-16 |
CA2228740A1 (en) | 1998-08-04 |
NL1005174C2 (en) | 1998-08-06 |
JPH10219168A (en) | 1998-08-18 |
DE69823399T2 (en) | 2005-05-04 |
DE69823399D1 (en) | 2004-06-03 |
EP0856565B1 (en) | 2004-04-28 |
JP4420988B2 (en) | 2010-02-24 |
CA2228740C (en) | 2006-09-05 |
US6071986A (en) | 2000-06-06 |
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